Four Key Pieces of Advice to My 20-Year-Old Self

About halfway through the first season of Shift Dialogs, we started asking our guests the same question: “What advice would you give your 20-year old self?”

Below are answers from a diverse group of folks: Nathan Blecharczyk of Airbnb, Debby Hopkins of Citi, Evan Williams of Medium, Marc Pritchard of P&G, and Bruce Aust of Nasdaq.

Asking all these folks their advice got me thinking about what I’d tell myself if I could go back 30 years, right about the time I was trying to figure out whether to work straight out of college, or continue my studies toward a PhD in Anthropology, a route I was seriously considering at the time (I ended up joining a startup …). If I had the chance to talk to my younger self, my advice would center on steering clear of decisions that I later rued. Here we go:

Let go when you know it’s time to let go. Over and over in my career and in my personal life, I’ve clung to a job, a company, or a person that was no longer working out. I knew in my heart it was over, but I felt obliged to continue?—?I didn’t want to be the guy who walked out, I felt duty-bound to be the captain on the bridge of a sinking ship, I was sure there had to be a way through or out of whatever predicament I found myself in. But the truth is, sometimes more people get hurt when you hold on for too long. An example is The Industry Standard, a company I founded in 1997, then lost to a Board vote during the dot com crash in 2001. Back in mid 2000, I knew I vehemently disagreed with my Board and my main investor, but I agreed to stay on regardless. I should have left when that disagreement became intractable, but I didn’t want to abandon my team. That led to a lot of pain for many people, who also remained at the company, and who ultimately were laid off. Bummer all around.

Identify your passions, and check in against them from time to time. I don’t rue my decision to pursue work instead of academia, but I regret not taking more time to explore the “life of the mind.” Had I written down the things that really excited me when I was 20 years old, then referred back to them from time to time, I’d have been far more in touch with what drove me, instead of taking whatever the next interesting challenge was that came my way. Thirty years ago, I’d have put “deep field work leading to publication of a book” as one of my passions, it was a major goal of mine early in life. And had I checked in against that goal, perhaps it’d not have taken me 20 years to publish my first book. And perhaps I’d have gotten to that second one a bit earlier….

Don’t be afraid of success. I was very fortunate in my early career?—?the first startup I co-founded, Wired, did extremely well. But I was terrified of that success, so much so, in fact, that when Wired was sold, I held on to the shares I was given for far, far too long. I remember the day those shares landed in my (newly created) account, and for months I watched them climb in value (this was the late 90s, when the dot com boom was really booming). Almost daily I’d wonder if it was time to simply cash out of my position, but that would have made my sweat equity real?—?and forced me to come to terms with what felt like unimaginable wealth. Instead, I let it ride…all the way down to about 15% of peak value (my wife finally made me sell, just as the shares were plummeting along with the rest of the market). So I’d love to tell my younger self: It’s OK to put some money in your jeans if you are fortunate enough to have that choice. Several times over my career I had an opportunity to generate wealth, but I hesitated, wondering if I really had earned the right, or feeling that pushing for that “big win” was too mercenary or selfish. My delays and vacillations cost my family significant opportunity, and forced me to seek funding from others for companies I might have started with my own resources.

There’s nothing wrong with asking dumb questions. Finally, I’d tell my younger self to never, ever be afraid to ask for help, and to always find ways to help other people. Several times I found myself in positions of leadership where I honestly had no idea what I was doing, but I felt embarrassed about asking for help. I’ve pretty much faked my way through several crises?—?and I’m quite sure I could have done better had I sought advice. Now that I’m older, I see this behavior over and over again in young founders?—?they’re in positions of leadership for the first time, and they think its their job to project certainty and self-confidence no matter what. I’ve now learned that there’s nothing better for your ability to sleep at night than to admit you have no clue?—?and to talk with someone who might help you get one. The flip side of this is to help as much as you possibly can?—?to always be open to answering those dumb questions that come your way. It’s an honor to help someone work through a difficult patch?—?and when you do, good things come your way.

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